Organic electroluminescence device and amine compound for organic electroluminescence device

ABSTRACT

An organic electroluminescence device (OLED) of an embodiment includes a first electrode, a hole transport region on the first electrode, an emission layer on the hole transport region, and an electron transport region on the emission layer. The hole transport region may include an amine compound represented by Formula 1, and the OLED may thereby exhibit high luminous efficiency:

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2020-0070839, filed on Jun. 11, 2020, the entirecontent of which is hereby incorporated by reference.

BACKGROUND 1. Field

One or more aspects of embodiments of the present disclosure relate toan organic electroluminescence device and an amine compound for theorganic electroluminescence device.

2. Description of the Related Art

Organic electroluminescence displays are being actively developed asimage display devices. Unlike liquid crystal display devices and/or thelike, an organic electroluminescence display is a so-calledself-luminescent display device, in which holes and electrons injectedfrom a first electrode and a second electrode recombine in an emissionlayer, and a luminescent material including an organic compound in theemission layer emits light to implement display.

In the application of an organic electroluminescence device to a displaydevice, an organic electroluminescence device having a low drivingvoltage, a high luminous efficiency, and/or a long service life isdesired, and new materials capable of stably attaining suchcharacteristics in an organic electroluminescence device are desired.

SUMMARY

One or more aspects of embodiments of the present disclosure aredirected toward an organic electroluminescence device having a longservice life and high efficiency, and an amine compound used therein.

One or more example embodiments of the present disclosure provide anamine compound represented by Formula 1:

In Formula 1, L₁ and L₂ may each independently be a direct linkage, asubstituted or unsubstituted arylene group having 6 to 30 ring-formingcarbon atoms, or a substituted or unsubstituted heteroarylene grouphaving 2 to 30 ring-forming carbon atoms, m and n may each independentlybe an integer of 0 to 2, Ar₁ and Ar₂ may each independently be asubstituted or unsubstituted aryl group having 6 to 30 ring-formingcarbon atoms or a substituted or unsubstituted heteroaryl group, R₁ toR₄ may each independently be a hydrogen atom, a deuterium atom, ahalogen atom, a cyano group, a substituted or unsubstituted alkyl grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 ring-forming carbon atoms, or a substituted orunsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,a and b may each independently be an integer of 0 to 4, and c and d mayeach independently be an integer of 0 to 5.

In an embodiment, the amine compound represented by Formula 1 may berepresented by Formula 2:

In Formula 2, Ar₁, Ar₂, L₁, R₁ to R₄, n, and a to d may eachindependently be the same as defined in Formula 1.

In an embodiment, the amine compound of Formula 2 may be represented byFormula 3:

In Formula 3, Ar₁, Ar₂, L₁, R₁ to R₄, n, and a to d may eachindependently be the same as defined in Formula 2.

In an embodiment, the amine compound represented by Formula 3 may berepresented by Formula 4-1 or Formula 4-2:

In Formula 4-1 and Formula 4-2, Ar₁, Ar₂, L₁, R₁ to R₄, n, and a to dmay each independently be the same as defined in Formula 3.

In an embodiment, the amine compound represented by Formula 3 may berepresented by Formula 4-3 or Formula 4-4:

In Formula 4-3 and Formula 4-4, Ar₁, Ar₂, L₁, R₁ to R₄, n, and a to dmay each independently be the same as defined in Formula 3.

In an embodiment, L₁ may be a direct linkage, a substituted orunsubstituted phenylene, or a substituted or unsubstituted naphthylene.

In an embodiment, L₁ may be represented by Formula 5:

In an embodiment, Ar₂ may be a substituted or unsubstituted aryl grouphaving 6 to 16 ring-forming carbon atoms.

In an embodiment, Ar₂ may be a substituted or unsubstituted phenylgroup, a substituted or unsubstituted naphthyl group, a substituted orunsubstituted biphenyl group, or a substituted or unsubstitutedphenanthrenyl group.

In an embodiment, Ar₂ may be a substituted or unsubstituteddibenzofuranyl group or a substituted or unsubstituted dibenzothiophenylgroup.

In an embodiment, Ar₁ may be represented by Formula 6:

In Formula 6, R₅ may be O or S, R₅ may be a hydrogen atom, a deuteriumatom, a halogen atom, a cyano group, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedaryl group having 6 to 30 ring-forming carbon atoms, or a substituted orunsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,and e may be an integer of 0 to 5.

In an embodiment, the amine compound represented by Formula 1 may be anyone selected from the compounds represented by Compound Group 1 (asindicated in the present disclosure).

One or more example embodiments of the present disclosure provide anorganic electroluminescence device including: a first electrode; a holetransport region disposed on the first electrode; an emission layerdisposed on the hole transport region; and an electron transport regiondisposed on the emission layer, wherein the hole transport regionincludes the amine compound represented by Formula 1.

In an embodiment, the hole transport region may include a hole injectionlayer disposed on the first electrode and the hole transport layerdisposed on the hole injection layer, wherein the hole injection layeror the hole transport layer may include the amine compound.

BRIEF DESCRIPTION OF THE DRAWINGS

The accompanying drawings are included to provide a furtherunderstanding of the present disclosure, and are incorporated in andconstitute a part of this specification. The drawings illustrate exampleembodiments of the present disclosure and, together with thedescription, serve to explain principles of the present disclosure. Inthe drawings:

FIG. 1 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment of the presentdisclosure;

FIG. 2 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment of the presentdisclosure;

FIG. 3 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment of the presentdisclosure; and

FIG. 4 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment of the presentdisclosure.

DETAILED DESCRIPTION

The present disclosure may have various modifications and may beembodied in different forms, and example embodiments will be explainedin detail with reference to the accompanying drawings. However, thepresent disclosure should not be construed as being limited to theembodiments set forth herein. Rather, all modifications, equivalents,and substituents that are included in the spirit and technical scope ofthe present disclosure should be included in the present disclosure.

In the present description, when an element (or a region, a layer, aportion, etc.) is referred to as being “on,” “connected to,” or “coupledto” another element, the element may be directly disposed on/connectedto/coupled to the other element, or a third element may be disposedtherebetween. When an element is referred to as being “directly on,”“directly connected to,” or “directly coupled to” another element, thereare no intervening elements present.

Like reference numerals refer to like elements throughout, andduplicative descriptions thereof may not be provided. Also, in thedrawings, thicknesses, ratios, and dimensions of elements areexaggerated for an effective description of technical contents.

The term “and/or” includes any and all combinations of one or more ofthe associated listed items.

It will be understood that, although the terms “first”, “second”, etc.may be used herein to describe various elements, these elements shouldnot be limited by these terms. These terms are only used to distinguishone element from another. For example, a first element could be termed asecond element, and, similarly, a second element could be termed a firstelement, without departing from the scope of example embodiments of thepresent disclosure. Terms used in their singular forms may include thecorresponding plural forms, unless the context clearly indicatesotherwise.

In addition, terms such as “below,” “lower,” “above,” “upper,” and/orthe like are used to describe the relationship of the configurationsshown in the drawings. The terms are used as relative concepts, and aredescribed with reference to the direction indicated in the drawings.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which the present disclosure pertains.It is also to be understood that terms defined in commonly useddictionaries should be interpreted as having meanings consistent withthe meanings in the context of the related art, unless expressly definedherein, and should not be interpreted in an ideal or overly formalsense.

It should be understood that the terms “have,” “includes,” “including,”“comprises,” and/or “comprising,” are intended to specify the presenceof stated features, integers, steps, operations, elements, components,or combinations thereof in the disclosure, but do not preclude thepresence or addition of one or more other features, integers, steps,operations, elements, components, or combinations thereof.

As used herein, expressions such as “at least one of,” “one of,” and“selected from,” when preceding a list of elements, modify the entirelist of elements and do not modify the individual elements of the list.Further, the use of “may” when describing embodiments of the presentdisclosure refers to “one or more embodiments of the presentdisclosure”.

Hereinafter, an organic electroluminescence device according to anembodiment of the present disclosure and a compound of an embodimentincluded therein will be described with reference to the accompanyingdrawings.

FIGS. 1 to 4 are cross-sectional views schematically illustratingorganic electroluminescence devices according to embodiments of thepresent disclosure. Referring to FIGS. 1 to 4, in each of organicelectroluminescence devices 10 according to embodiments, a firstelectrode EL1 and a second electrode EL2 are disposed to face eachother, and an emission layer EML may be disposed between the firstelectrode EL1 and the second electrode EL2.

In some embodiments, each of the organic electroluminescence devices 10of embodiments may further include a plurality of functional layersbetween the first electrode EL1 and the second electrode EL2 in additionto the emission layer EML. The plurality of functional layers mayinclude a hole transport region HTR and an electron transport regionETR. For example, each of the organic electroluminescence devices 10according to embodiments may include the first electrode EL1, the holetransport region HTR, the emission layer EML, the electron transportregion ETR, and the second electrode EL2 that are sequentially stacked.In some embodiments, the organic electroluminescence device 10 of anembodiment may include a capping layer CPL disposed on the secondelectrode EL2.

The organic electroluminescence device 10 of an embodiment may includean amine compound of an embodiment, which will be described later, inthe hole transfer region HTR disposed between the first electrode EL1and the second electrode EL2. However, embodiments of the presentdisclosure are not limited thereto, and the organic electroluminescencedevice 10 of an embodiment may include a compound according to anembodiment, which will be described later, in the emission layer EML orelectron transport region ETR, or in the capping layer CPL disposed onthe second electrode EL2.

Compared to FIG. 1, FIG. 2 illustrates a cross-sectional view of anorganic electroluminescence device 10 of an embodiment, in which thehole transport region HTR includes a hole injection layer HIL and a holetransport layer HTL, and the electron transport region ETR includes anelectron injection layer EIL and an electron transport layer ETL.Compared to FIG. 1, FIG. 3 illustrates a cross-sectional view of anorganic electroluminescence device 10 of an embodiment, in which thehole transport region HTR includes the hole injection layer HIL, thehole transport layer HTL, and an electron blocking layer EBL, and theelectron transport region ETR includes the electron injection layer EIL,the electron transport layer ETL, and a hole blocking layer HBL.Compared to FIG. 2, FIG. 4 illustrates a cross-sectional view of anorganic electroluminescence device 10 of an embodiment including acapping layer CPL disposed on the second electrode EL2.

The first electrode EL1 may have conductivity. The first electrode EUmay be formed of a metal alloy or a conductive compound. The firstelectrode EU may be a pixel electrode or positive electrode. The firstelectrode EL1 may be a transmissive electrode, a transflectiveelectrode, or a reflective electrode. When the first electrode EL1 is atransmissive electrode, the first electrode EL1 may include atransparent metal oxide (such as indium tin oxide (ITO), indium zincoxide (IZO), zinc oxide (ZnO), and/or indium tin zinc oxide (ITZO)).When the first electrode EL1 is a transflective electrode or areflective electrode, the first electrode EL1 may include silver (Ag),magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium(Pd), gold (Au), nickel (Ni, neodymium (Nd), iridium (Ir), chromium(Cr), lithium (L₁), calcium (Ca), LiF/Ca, LiF/AI, molybdenum (Mo),titanium (Ti), a compound thereof, or a mixture thereof (e.g., a mixtureof Ag and Mg). In some embodiments, the first electrode EL1 may have amultilayer structure including a reflective layer or a transflectivelayer formed of the above-described materials, and a transparentconductive layer formed of ITO, IZO, ZnO, ITZO, etc. For example, thefirst electrode EU may have a three-layer structure of ITO/Ag/ITO, butembodiments of the present disclosure are not limited thereto. Thethickness of the first electrode EU may be about 1,000 Å to about 10,000Å, for example, about 1,000 Å to about 3,000 Å.

The hole transport region HTR is disposed on the first electrode EL1.The hole transport region HTR may include at least one of a holeinjection layer HIL, a hole transport layer HTL, a hole buffer layer, oran electron blocking layer.

The hole transport region HTR may have (e.g., be) a single layer formedof (e.g., consisting of) a single material, a single layer formed of aplurality of different materials, or a multilayer structure including aplurality of layers formed of a plurality of different materials.

For example, the hole transport region HTR may have (e.g., be) a singlelayer structure of a hole injection layer HIL or a hole transport layerHTL, or may have (e.g., be) a single layer structure formed of a holeinjection material and a hole transport material. In some embodiments,the hole transport region HTR may have a single layer structure formedof a plurality of different materials, or a structure in which a holeinjection layer HIL/hole transport layer HTL, a hole injection layerHIL/hole transport layer HTL/hole buffer layer, a hole injection layerHIL/hole buffer layer, a hole transport layer HTL/hole buffer layer, ora hole injection layer HIL/hole transport layer HTL/electron blockinglayer EBL are stacked in order from the first electrode EL1, butembodiments are not limited thereto.

The hole transport region HTR may be formed by utilizing any suitablemethod (such as a vacuum deposition method, a spin coating method, acast method, a Langmuir-Blodgett (LB) method, an inkjet printing method,a laser printing method, and/or a laser induced thermal imaging (LITI)method).

In an embodiment, the hole transport region HTR may include the aminecompound according to the present disclosure.

In the description, the term “substituted or unsubstituted” may indicatethat one (e.g., a group or atom) is unsubstituted, or is substitutedwith at least one substituent selected from the group consisting of adeuterium atom, a halogen atom, a cyano group, a nitro group, a silylgroup, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, acarbonyl group, a boron group, a phosphine oxide group, a phosphinesulfide group, an alkyl group, an alkenyl group, an alkoxy group, ahydrocarbon ring group, an aryl group, and a heterocyclic group. Each ofthe example substituents above may be further substituted orunsubstituted. For example, a biphenyl group may be interpreted as anamed aryl group, or as a phenyl group substituted with a phenyl group.

Non-limiting examples of the halogen atom include a fluorine atom, achlorine atom, a bromine atom, and an iodine atom.

In the description, the alkyl group may be a linear, branched or cyclictype alkyl group. The number of carbons in the alkyl group may be 1 to50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl groupinclude a methyl group, an ethyl group, an n-propyl group, an isopropylgroup, an n-butyl group, an s-butyl group, a t-butyl group, an i-butylgroup, a 2-ethylbutyl group, a 3,3-dimethylbutyl group, an n-pentylgroup, an i-pentyl group, a neopentyl group, a t-pentyl group, acyclopentyl group, a 1-methylpentyl group, a 3-methylpentyl group, a2-ethylpentyl group, a 4-methyl-2-pentyl group, an n-hexyl group, a1-methylhexyl group, a 2-ethylhexyl group, a 2-butylhexyl group, acyclohexyl group, a 4-methylcyclohexyl group, a 4-t-butylcyclohexylgroup, an n-heptyl group, a 1-methylheptyl group, a 2,2-dimethylheptylgroup, a 2-ethylheptyl group, a 2-butylheptyl group, an n-octyl group, at-octyl group, a 2-ethyloctyl group, a 2-butyloctyl group, a2-hexyloctyl group, a 3,7-dimethyloctyl group, a cyclooctyl group, ann-nonyl group, an n-decyl group, an adamantyl group, a 2-ethyldecylgroup, a 2-butyldecyl group, a 2-hexyldecyl group, a 2-octyldecyl group,an n-undecyl group, an n-dodecyl group, a 2-ethyldodecyl group, a2-butyldodecyl group, a 2-hexyldocecyl group, a 2-octyldodecyl group, ann-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, ann-hexadecyl group, a 2-ethylhexadecyl group, a 2-butylhexadecyl group, a2-hexylhexadecyl group, a 2-octylhexadecyl group, an n-heptadecyl group,an n-octadecyl group, an n-nonadecyl group, an n-eicosyl group, a2-ethyleicosyl group, a 2-butyleicosyl group, a 2-hexyleicosyl group, a2-octyleicosyl group, an n-henicosyl group, an n-docosyl group, ann-tricosyl group, an n-tetracosyl group, an n-pentacosyl group, ann-hexacosyl group, an n-heptacosyl group, an n-octacosyl group, ann-nonacosyl group, an n-triacontyl group, etc., but embodiments of thepresent disclosure are not limited thereto.

In the description, the term “alkenyl group” refers to a hydrocarbongroup including at least one carbon-carbon double bond in the middle orat the terminal end of an alkyl group having 2 or more carbon atoms. Thealkenyl group may be linear or branched. The number of carbon atoms isnot limited, and for example may be 2 to 30, 2 to 20, or 2 to 10.Examples of the alkenyl group include a vinyl group, a 1-butenyl group,a 1-pentenyl group, a 1,3-butadienyl aryl group, a styrenyl group, astyryl vinyl group, etc., but embodiments of the present disclosure arenot limited thereto.

In the description, the term “alkynyl group” refers to a hydrocarbongroup including at least one carbon-carbon triple bond in the middle orat the terminal end of an alkyl group having 2 or more carbon atoms. Thealkynyl group may be linear or branched. The number of carbon atoms isnot limited, and for example, may be 2 to 30, 2 to 20, or 2 to 10.Examples of the alkynyl group include an ethynyl group, a propynylgroup, etc., but are not limited thereto.

In the description, a hydrocarbon ring group may be any functional groupor substituent derived from an aliphatic hydrocarbon ring, or anyfunctional group or substituent derived from an aromatic hydrocarbonring. The number of ring-forming carbon atoms in the hydrocarbon ringgroup may be 5 to 60, 5 to 30, or 5 to 20.

In the description, the term “aryl group” refers to any functional groupor substituent derived from an aromatic hydrocarbon ring. The aryl groupmay be a monocyclic aryl group or a polycyclic aryl group. The number ofring-forming carbon atoms in the aryl group may be 6 to 30, 6 to 20, or6 to 15. Examples of the aryl group include a phenyl group, a naphthylgroup, a fluorenyl group, an anthracenyl group, a phenanthryl group, abiphenyl group, a terphenyl group, a quaterphenyl group, a quinquephenylgroup, a sexiphenyl group, a triphenylenyl group, a pyrenyl group, abenzofluoranthenyl group, a chrysenyl group, etc., but embodiments ofthe present disclosure are not limited thereto.

In the description, the fluorenyl group may be substituted, and twosubstituents may be combined with each other to form a spiro structure.Examples of the substituted fluorenyl group are as follows However, anembodiment of the present disclosure is not limited thereto.

In the description, the term “heterocyclic group” refers to anyfunctional group or substituent derived from a ring containing at leastone of boron (B), oxygen (O), nitrogen (N), phosphorus (P), silicon(Si), or sulfur (S) as a hetero atom. When the heterocyclic groupcontains two or more hetero atoms, the two or more hetero atoms may bethe same as or different from each other. The heterocyclic group may bean aliphatic heterocyclic group or an aromatic heterocyclic group. Thearomatic heterocyclic group may be a heteroaryl group. The aliphaticheterocycle and aromatic heterocycle may be monocyclic or polycyclic.

In the description, the aliphatic heterocyclic group may include atleast one of B, O, N, P, Si, or S as a hetero atom. The number ofring-forming carbon atoms in the aliphatic heterocyclic group may be 2to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic groupinclude an oxirane group, a thiirane group, a pyrrolidine group, apiperidine group, a tetrahydrofuran group, a tetrahydrothiophene group,a thiane group, a tetrahydropyran group, a 1,4-dioxane group, etc., butare not limited to thereto.

In the description, the heteroaryl group may include at least one of B,O, N, P, Si, or S as a heteroatom. When the heteroaryl group containstwo or more heteroatoms, the two or more heteroatoms may be the same asor different from each other. The heteroaryl group may be a monocyclicheteroaryl group or a polycyclic heteroaryl group. The number ofring-forming carbon atoms in the heteroaryl group may be 2 to 30, 2 to20, or 2 to 10. Examples of the heteroaryl group include a thiophenegroup, a furan group, a pyrrole group, an imidazole group, a triazolegroup, a pyridine group, a bipyridine group, a pyrimidine group, atriazine group, a triazole group, an acridyl group, a pyridazine group,a pyrazinyl group, a quinoline group, a quinazoline group, a quinoxalinegroup, a phenoxazine group, a phthalazine group, a pyrido pyrimidinegroup, a pyrido pyrazine group, a pyrazino pyrazine group, anisoquinoline group, an indole group, a carbazole group, anN-arylcarbazole group, an N-heteroarylcarbazole group, anN-alkylcarbazole group, a benzoxazole group, a benzimidazole group, abenzothiazole group, a benzocarbazole group, a benzothiophene group, adibenzothiophene group, a thienothiophene group, a benzofuran group, aphenanthroline group, a thiazole group, an isoxazole group, an oxazolegroup, an oxadiazolyl group, a thiadiazole group, a phenothiazine group,a dibenzosilole group, a dibenzofuran group, etc., but embodiments ofthe present disclosure are not limited thereto.

In the description, the term “thio group” may refer to an alkylthiogroup or an arylthio group. For example, the thio group includes asulfur atom bonded to an alkyl group or an aryl group as defined above.Examples of a thiol group include a methylthio group, an ethylthiogroup, a propylthio group, a pentylthio group, a hexylthio group, anoctylthio group, a dodecylthio group, a cyclopentylthio group, acyclohexylthio group, a phenylthio group, a naphthylthio group, butembodiments of the present disclosure are not limited thereto.

The term “oxy group” refers to a group including an oxygen atom bondedto an alkyl group or an aryl group as defined above. The oxy group maybe an alkoxy group or an aryl oxy group. The alkoxy group may include alinear, branched or cyclic alkyl chain. The number of carbon atoms inthe alkoxy group is not particularly limited, but for example, may be 1to 20 or 1 to 10. Examples of an oxy group include methoxy, ethoxy,n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy,decyloxy, benzyloxy, etc., but embodiments of the present disclosure arenot limited thereto.

In the description, the alkyl group included in an alkylthio group, analkylsulfoxy group, an alkylaryl group, an alkylamino group, an alkylboron group, an alkyl silyl group, and an alkyl amine group is the sameas the alkyl group described above.

In the description, the aryl group included in an aryloxy group, anarylthio group, an arylsulfoxy group, an arylamino group, an arylborongroup, an arylsilyl group, an arylamine group is the same as the arylgroup described above.

In the description, the term “direct linkage” may refer to a singlebond.

In the description, “

” refers to a connecting point to another group or moiety.

The amine compound according to an embodiment of the present disclosureis represented by Formula 1:

In Formula 1, L₁ and L₂ may each independently be a direct linkage, asubstituted or unsubstituted arylene group having 6 to 30 ring-formingcarbon atoms, or a substituted or unsubstituted heteroarylene grouphaving 2 to 30 ring-forming carbon atoms.

In Formula 1, m may be an integer of 0 to 2, and when m is 2, aplurality of L₂'s are the same as or different from each other.

In Formula 1, n may be an integer of 0 to 2, and when n is 2, aplurality of L₁'s are the same as or different from each other.

In Formula 1, Ar₁ and Ar₂ may each independently be a substituted orunsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or asubstituted or unsubstituted heteroaryl group having 2 to 30ring-forming carbon atoms.

In Formula 1, R₁ to R₄ may each independently be a hydrogen atom, adeuterium atom, a halogen atom, a cyano group, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or asubstituted or unsubstituted heteroaryl group having 2 to 30ring-forming carbon atoms.

In Formula 1, a may be an integer of 0 to 4, and when a is 2 or more, aplurality of R₁'s are the same as or different from each other.

In Formula 1, b may be an integer of 0 to 4, and when b is 2 or more, aplurality of R₂'s are the same as or different from each other.

In Formula 1, c may be an integer of 0 to 5, and when c is 2 or more, aplurality of R₃'s are the same as or different from each other.

In Formula 1, d may be an integer of 0 to 5, and when d is 2 or more, aplurality of R₄'s are the same as or different from each other.

In an embodiment, L₂ in Formula 1 may be a direct linkage. In anembodiment, the amine compound represented by Formula 1 may berepresented by Formula 2:

In Formula 2, Ar₁, Ar₂, L₁, R₁ to R₄, n, and a to d may eachindependently be the same as defined in Formula 1.

In an embodiment, the nitrogen of the amine group in Formula 1 may bebonded to a phenylene at a para-position with respect to the cyclohexylgroup. In an embodiment, the amine compound represented by Formula 2 maybe represented by Formula 3:

In Formula 3, Ar₁, Ar₂, L₁, R₁ to R₄, n, and a to d may eachindependently be the same as defined in Formula 2.

In an embodiment, the amine compound represented by Formula 3 may berepresented by Formula 4-1 or Formula 4-2:

In Formula 4-1 and Formula 4-2, Ar₁, Ar₂, L₁, R₁ to R₄, n, and a to dmay each independently be the same as defined in Formula 3.

In an embodiment, the amine compound represented by Formula 3 may berepresented by Formula 4-3 or Formula 4-4:

In Formula 4-3 and Formula 4-4, Ar₁, Ar₂, L₁, R₁ to R₄, n, and a to dmay each independently be the same as defined in Formula 3.

In an embodiment, L₁ of the amine compound may be a direct linkage, asubstituted or unsubstituted phenylene, or a substituted orunsubstituted naphthylene.

In an embodiment, when L₁ of the amine compound is a phenylene, L₁ maybe represented by Formula 5:

In Formula 5, “

” refers to a position to be connected with the carbazole group or thenitrogen of the amine group.

In an embodiment, Ar₂ of the amine compound may be a substituted orunsubstituted aryl group having 6 to 16 ring-forming carbon atoms.

In an embodiment, Ar₂ of the amine compound may be a substituted orunsubstituted phenyl group, a substituted or unsubstituted naphthylgroup, a substituted or unsubstituted biphenyl group, or a substitutedor unsubstituted phenanthrenyl group.

In an embodiment, Ar₂ of the amine compound may be a substituted orunsubstituted carbazolyl group. In an embodiment, Ar₂ of the aminecompound may be a substituted or unsubstituted dibenzofuranyl group or asubstituted or unsubstituted dibenzothiophenyl group.

In an embodiment, the amine compound may not include a substituentcontaining N (e.g., may be substituted only with substituents excludingan N atom). For example, N other than the N atoms represented in Formula1 may be not included (e.g., Formula 1 may not include any other N atomsbesides the amine group N and the carbazolyl group N).

In an embodiment, An of the amine compound may be represented by Formula6:

In Formula 6, R₅ may be a hydrogen atom, a deuterium atom, a halogenatom, a cyano group, a substituted or unsubstituted alkyl group having 1to 20 carbon atoms, a substituted or unsubstituted aryl group having 6to 30 ring-forming carbon atoms, or a substituted or unsubstitutedheteroaryl group having 2 to 30 ring-forming carbon atoms.

In Formula 6, e may be an integer of 0 to 5, and when e is an integer of2 or more, a plurality of R₅'s are the same as or different from eachother.

In Formula 6, “

” refers to a position to be connected with the nitrogen of a carbazolegroup.

In an embodiment, the amine compound represented by Formula 1 may be anyone selected from the compounds represented by Compound Group 1.However, embodiments of the present disclosure are not limited thereto.

The above-described amine compound may be used in the organicelectroluminescence device 10 of an embodiment to improve the efficiencyand/or service life (e.g., life span) of the organic electroluminescencedevice. For example, the above-described amine compound may be used inthe hole transport region HTR of the organic electroluminescence device10 of an embodiment to improve the luminous efficiency, electrontransport properties, and/or service life of the organicelectroluminescence device.

An organic electroluminescence device according to an embodiment of thepresent disclosure will be further described with reference to FIGS. 1to 3.

When the hole transport region HTR is a multilayer structure having aplurality of layers, at least one layer of the plurality of layers mayinclude the amine compound represented by Formula 1. For example, thehole transport region HTR may include the hole injection layer HILdisposed on the first electrode EL1 and the hole transport layer HTLdisposed on the hole injection layer HIL, wherein the hole injectionlayer HIL and/or the hole transport layer HTL may include the aminecompound represented by Formula 1.

The hole transport region HTR may include one or two or more of theamine compounds represented by Formula 1. For example, the holetransport region HTR may include at least one selected from among thecompounds represented by Compound Groups 1 as described above.

However, embodiments of the present disclosure are not limited thereto,and the hole injection layer HIL and the hole transport layer HTL mayfurther include any suitable material.

The hole injection layer HIL may further include, for example, aphthalocyanine compound (such as copper phthalocyanine),N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine(DNTPD), 4,4′,4″-[tris(3-methylphenyl)phenylamino]triphenylamine](m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA),4,4′,4″-tris{N,-(2-naphthyl) N-phenylamino)-triphenylamine (2-TNATA),poly(3,4-ethylene dioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS),polyaniline/dodecylbenzene sulfonic acid (PANI/DBSA),polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), N,N′-di(naphthalene-1-yl)-N,N′-diphenyl-benzidine(NPD), triphenylamine-containing polyether ketone (TPAPEK),4-isopropyl-4′-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate,dipyrazino[2,3-f: 2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile(HAT-CN), etc.

The hole transport layer HTL may further include, for example, carbazolederivatives (such as N-phenyl carbazole and/or polyvinyl carbazole),fluorene derivatives,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), triphenylamine derivatives (such as4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA)),N,N′-di(naphthalen-1-yl)-N,N′-diphenyl-benzidine (NPB),4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl]benzenamine] (TAPC),4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD),1,3-bis(N-carbazolyl)benzene (mCP), etc.

The electron blocking layer EBL may include, for example, carbazolederivatives (such as N-phenyl carbazole and/or polyvinyl carbazole),fluorene derivatives,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), triphenylamine derivatives (such as4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA)),N,N′-di(naphthalen-1-yl)-N,N′-diphenyl-benzidine (NPB),4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenam ine] (TAPC),4,4′-bis[N,N-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD),9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi),9-phenyl-9H-3,9′-biscarbazole (CCP), 1,3-bis(N-carbazolyl)benzene (mCP),1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene (mCDP), etc.

The thickness of the hole transport region HTR may be about 100 Å toabout 10,000 Å, for example, about 100 Å to about 5,000 Å. The thicknessof the hole injection region HIL may be, for example, about 30 Å toabout 1,000 Å, and the thickness of the hole transport layer HTL may beabout 30 Å to about 1,000 Å. For example, the thickness of the electronblocking layer EBL may be about 10 Å to about 1,000 Å. When thethicknesses of the hole transport region HTR, the hole injection layerHIL, the hole transport layer HTL and the electron blocking layer EBLsatisfy the above-described ranges, satisfactory hole transportproperties may be achieved without a substantial increase in drivingvoltage.

The hole transport region HTR may further include, in addition to theabove-described materials, a charge generating material to increaseconductivity. The charge generating material may be dispersedsubstantially uniformly or non-uniformly in the hole transport regionHTR. The charge generating material may be, for example, a p-dopant. Thep-dopant may be a quinone derivative, a metal oxide, or a cyanogroup-containing compound, but embodiments of the present disclosure arenot limited thereto. Non-limiting examples of the p-dopant includequinone derivatives such as tetracyanoquinodimethane (TCNQ) and/or2,3,5,6-tetrafluoro-7,7′,8,8′-tetracyanoquinodimethane (F4-TCNQ), metaloxides such as tungsten oxide and/or molybdenum oxide, etc., butembodiments of the present disclosure are not limited thereto.

As described above, the hole transport region HTR may further include atleast one of a hole buffer layer or an electron blocking layer EBL inaddition to the hole injection layer HIL and the hole transport layerHTL. The hole buffer layer, may compensate for a resonance distance ofthe wavelength of light emitted from an emission layer EML, and mayincrease the light emission efficiency of the device. Materials that maybe included in the hole transport region HTR may be included in the holebuffer layer. The electron blocking layer EBL may prevent or reduceelectrons from being injected from the electron transport region ETR tothe hole transport region HTR.

The emission layer EML is disposed on the hole transport region HTR. Thethickness of the emission layer EML may be, for example, about 100 Å toabout 1,000 Å or about 100 Å to about 300 Å. The emission layer EML mayhave (e.g., be) a single layer formed of (e.g., consisting of) a singlematerial, a single layer formed of a plurality of different materials,or a multilayer structure having a plurality of layers formed of aplurality of different materials.

The emission layer may emit one of red, green, blue, white, yellow orcyan light. The emission layer EML may include a fluorescence-emittingmaterial and/or a phosphorescence-emitting material.

Any suitable material in the art may be used in the emission layer EML,for example, one selected from fluoranthene derivatives, pyrenederivatives, arylacetylene derivatives, anthracene derivatives, fluorenederivatives, perylene derivatives, chrysene derivatives, etc. In someembodiments, the host materials may include pyrene derivatives, perylenederivatives, and/or anthracene derivatives. For example, anthracenederivatives represented by Formula 10 may be used as the host materialsof the emission layer EML:

In Formula 10, W₁ to W₄ may each independently be a hydrogen atom, adeuterium atom, a halogen atom, a substituted or unsubstituted silylgroup, a substituted or unsubstituted alkyl group having 1 to 20 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30ring-forming carbon atoms, or a substituted or unsubstituted heteroarylgroup having 2 to 30 ring-forming carbon atoms, or may be bonded to anadjacent group to form a ring, m1 and m2 are each independently aninteger of 0 to 4, and m3 and m4 are each independently an integer of 0to 5.

When m1 is 1, W₁ may not be a hydrogen atom, when m2 is 1, W₂ may not bea hydrogen atom, when m3 is 1, W₃ may not be a hydrogen atom, and whenm4 is 1, W₄ may not be a hydrogen atom.

When m1 is 2 or more, a plurality of W₁'s may be the same or different.When m2 is 2 or more, a plurality of W₂'s may be the same or different.When m3 is 2 or more, a plurality of W₃'s may be the same or different.When m4 is 2 or more, a plurality of W₄'s may be the same or different.

The compound represented by Formula 10 may include, for example, acompound represented by (selected from) the following structures.However, the compound represented by Formula 10 is not limited thereto.

The emission layer EML may further include a dopant, and any suitablematerial may be used as the dopant. For example, at least one of astyryl derivative (for example,1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB),4-(di-p-tolylamino)-4″-[(di-p-tolylamino)styryl]stilbene (DPAVB),4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi) and/orN-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenz enamine(N-BDAVBi)), perylene and/or a derivative thereof (for example,2,5,8,11-tetra-t-butylperylene (TBPe)), and/or pyrene and/or aderivative thereof (for example, 1,1-dipyrene, 1,4-dipyrenylbenzene,1,4-bis(N,N-diphenylamino)pyrene, 1,6-bis(N,N-diphenylamino)pyrene),2,5,8,11-tetra-t-butylperylene (TBP), and/or1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBi)) may be used as adopant, but embodiments of the present disclosure are not limitedthereto.

The emission layer EML may further include any suitable material in theart as a host material. For example, the emission layer EML may include,as a host material, at least one of bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4′-bis(carbazol-9-yl)biphenyl (CBP),1,3-bis(carbazol-9-yl)benzene (mCP),2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF),4,4′,4″-tris(carbazol-9-yl)-triphenylamine (TCTA), or1,3,5-tris(1-phenyl-1H-benz[d]imidazole-2-yl)benzene (TPBi). However,embodiments of the present disclosure are not limited thereto, and forexample, tris(8-hydroxyquinolino)aluminum (Alq₃),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), poly(N-vinylcarbazole (PVK),9,10-di(naphthalene-2-yl)anthracene (ADN),4,4′,4″-tris(carbazol-9-yl)-triphenylamine (TCTA),1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBi),2-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), distyrylarylene(DSA), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene(UGH2), hexaphenylcyclotrisiloxane (DPSiO₃), octaphenylcyclotetrasiloxane (DPSiO₄), 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF), etc.may be used as a host material.

In an embodiment, the emission layer EML may include any suitablephosphorescence dopant material in the art. For example, a metal complexincluding iridium (Ir), platinum (Pt), osmium (Os), aurum (Au), titanium(Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and/orthulium (Tm) may be used as a phosphorescence dopant. For example,iridium(III) bis(4,6-difluorophenylpyridinato-N,C2′)picolinate (Flrpic),bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III) (Fir6), and/or platinum octaethyl porphyrin (PtOEP) may be used asa phosphorescence dopant. However, embodiments of the present disclosureare not limited thereto.

The emission layer EML may further include any suitable phosphorescencehost material in the art, for example,bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS).

When the emission layer EML is to emit red light, the emission layer EMLmay further include, for example, a fluorescent material includingtris(dibenzoylmethanato)phenanthoroline europium (PBD: Eu(DBM)₃(Phen))or perylene. When the emission layer EML is to emit red light, a dopantincluded in the emission layer EML may be, for example, a metal complexand/or an organometallic complex (such asbis(1-phenylisoquinoline)acetylacetonate iridium (PIQIr(acac)),bis(1-phenylquinoline)acetylacetonate iridium (PQIr(acac)),tris(1-phenylquinoline)iridium (PQIr), and/or octaethylporphyrinplatinum (PtOEP)), rubrene and/or a derivative thereof, and/or4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM)and/or a derivative thereof.

When the emission layer EML is to emit green light, the emission layerEML may further include, for example, a fluorescent material includingtris(8-hydroxyquinolino)aluminum (Alq₃). When the emission layer EML isto emit green light, a dopant included in the emission layer EML may be,for example, selected from a metal complex or an organometallic complex(such as fac-tris(2-phenylpyridine) iridium (Ir(ppy)₃)) and coumarinand/or a derivative thereof.

When the emission layer EML is to emit blue light, the emission layerEML may further include, for example, a fluorescent material includingone selected from the group consisting of spiro-DPVBi, spiro-6P,distyryl-benzene (DSB), distyryl-arylene (DSA), a polyfluorene(PFO)-based polymer, and a poly(p-phenylene vinylene (PPV)-basedpolymer. When the emission layer EML is to emit blue light, a dopantincluded in the emission layer EML may be, for example, selected from ametal complex and/or an organometallic complex (such as(4,6-F2ppy)₂Irpic), and/or perylene and a derivative thereof.

In some embodiments, the organic electroluminescence device 10 of anembodiment may include a plurality of emission layers. The plurality ofemission layers may be sequentially stacked, and for example, theorganic electroluminescence device 10 including the plurality ofemission layers may be to emit white light. The organicelectroluminescence device including a plurality of emission layers maybe an organic electroluminescence device having a tandem structure.

The electron transport region ETR is disposed on the emission layer EML.The electron transport region ETR may include at least one of a holeblocking layer HBL, an electron transport layer ETL, or an electroninjection layer EIL, but embodiments are not limited thereto.

The electron transport region ETR may have (e.g., be) a single layerformed of (e.g., consisting of) a single material, a single layer formedof a plurality of different materials, or a multilayer structureincluding a plurality of layers formed of a plurality of differentmaterials.

For example, the electron transport region ETR may have (e.g., be) asingle layer structure of an electron injection layer EIL or an electrontransport layer ETL, or may have (e.g., be) a single layer structureformed of an electron injection material and an electron transportmaterial. In some embodiments, the electron transport region ETR mayhave a single layer structure formed of a plurality of differentmaterials, or may have a structure in which an electron transport layerETL/electron injection layer EIL and a hole blocking layer HBL/electrontransport layer ETL/electron injection layer EIL are stacked in orderfrom the emission layer EML, but is not limited thereto. The thicknessof the electron transport region ETR may be, for example, about 1,000 Åto about 1,500 Å.

The electron transport region ETR in the organic electroluminescencedevice 10 of an embodiment may include an amine compound according to anembodiment of the present disclosure. In another embodiment, theelectron injection layer EIL or the electron transport layer ETL mayinclude the amine compound according to an embodiment of the presentdisclosure.

The electron transport region ETR may be formed by utilizing anysuitable method (such as a vacuum deposition method, a spin coatingmethod, a cast method, a Langmuir-Blodgett (LB) method, an inkjetprinting method, a laser printing method, a laser induced thermalimaging (LITI) method, etc.)

The electron transport region ETR may include any suitable material inthe art. When the electron transport region ETR includes the electrontransport layer ETL, the electron transport region ETR may include ananthracene-based compound. However, embodiments of the presentdisclosure are not limited thereto, and the electron transport regionmay include, for example, tris(8-hydroxyquinolinato)aluminum (Alq₃),1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene,2,4,6-tris(3′-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine,2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene,1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi),2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen),3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ),4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ),2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD),bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum(BAlq), beryllium bis(benzoquinolin-10-olate (Bebq₂),9,10-di(naphthalene-2-yl)anthracene (ADN),1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (B3PyPB), or a mixturethereof. The thickness of the electron transport layers ETL may be about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layers ETL satisfies theabove-described ranges, satisfactory electron transport characteristicsmay be obtained without a substantial increase in driving voltage.

When the electron transport region ETR includes the electron injectionlayer EIL, the electron transport region ETR may be formed utilizing ametal halide (such as LiF, NaCl, CsF, RbCl, RbI, and/or Cul), alanthanide metal (such as Yb), a metal oxide (such as Li₂O and/or BaO),8-hydroxyl-lithium quinolate (LiQ), etc., but embodiments of the presentdisclosure are not limited thereto. The electron injection layer EIL mayalso be formed of a mixture material of an electron transport materialand an insulating organometallic salt. The organometallic salt may be amaterial having an energy band gap of about 4 eV or more. Theorganometallic salt may include, for example, metal acetates, metalbenzoates, metal acetoacetates, metal acetylacetonates, and/or metalstearates. The thickness of the electron injection layer EIL may beabout 1 Å to about 100 Å, and about 3 Å to about 90 Å. When thethickness of the electron injection layers EIL satisfies theabove-described ranges, satisfactory electron injection properties maybe obtained without a substantial increase in driving voltage.

The electron transport region ETR may include a hole blocking layer HBLas described above. The hole blocking layer HBL may include, but is notlimited to, for example, at least one of2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), or4,7-diphenyl-1,10-phenanthroline (Bphen).

The second electrode EL2 is disposed on the electron transport regionETR. The second electrode EL2 may be a common electrode or a negativeelectrode. The second electrode EL2 may be a transmissive electrode, atransflective electrode, or a reflective electrode. When the secondelectrode EL2 is a transmissive electrode, the second electrode EL2 maybe formed of a transparent metal oxide, for example, ITO, IZO, ZnO,ITZO, etc.

When the second electrode EL2 is a transflective electrode or areflective electrode, the second electrode EL2 may include Ag, Mg, Cu,Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, acompound thereof, or a mixture thereof (for example, a mixture of Ag andMg). In some embodiments, the first electrode EL1 may have a multilayerstructure including a reflective layer or a transflective layer formedof the above-described materials, and a transparent conductive layerformed of ITO, IZO, ZnO, ITZO, etc.

In some embodiments, the second electrode EL2 may be connected with anauxiliary electrode. When the second electrode EL2 is connected to theauxiliary electrode, the resistance of the second electrode EL2 maydecrease.

Referring to FIG. 4, the organic electroluminescence device 10 accordingto an embodiment may further include a capping layer CPL on the secondelectrode EL2. The capping layer CPL may include a multilayer or asingle layer. In an embodiment, the capping layer CPL may be an organiclayer or an inorganic layer. For example, when the capping layer CPLincludes an inorganic material, the inorganic material may include analkaline metal compound (such as LiF), an alkaline earth metal compound(such as MgF₂, SiON, SiN_(x), and/or SiO_(y)), etc.

For example, when the capping layer CPL includes an organic material,the capping layer CPL may include the amine compound according to anembodiment. However, embodiments of the present disclosure are notlimited thereto, and the capping layer CPL may include α-NPD, NPB, TPD,m-MTDATA, Alq₃, CuPc,N4,N4,N4′,N4′-tetra(biphenyl-4-yl)biphenyl-4,4′-diamine (TPD15),4,4′,4″-tris(carbazol-9-yl)triphenylamine (TCTA), etc., or an epoxyresin, or an acrylate (such as methacrylate). However, embodiments ofthe present disclosure are not limited thereto, and the organic materialmay include at least one selected from Compounds P1 to P5.

The organic electroluminescence device 10 according to an embodiment ofthe present disclosure may include the amine compound represented byFormula 1 as described above to thereby exhibit excellent luminousefficiency and/or long service life characteristics. The organicelectroluminescence device 10 of an embodiment may achieve highefficiency and/or long service life characteristics in a blue wavelengthregion.

Hereinafter, a compound according to an embodiment of the presentdisclosure and an organic electroluminescence device of an embodimentwill be described in more detail with reference to Examples andComparative Examples. The Examples are illustrated only to facilitateunderstanding of this present disclosure, and the scope of the presentdisclosure is not limited thereto.

EXAMPLES

(Synthesis of Amine Compound)

In the following descriptions, a synthetic method of an amine compoundis provided as an example, but the synthetic method according to anembodiment of the present disclosure is not limited to the followingexamples.

1. Synthesis of Compound 1

Synthesis of Intermediate 1-1

1,4-dibromobenzene (2.36 g, 10 mmol) was dissolved in THF (20 mL),n-BuLi was added thereto at −78° C., and the mixture was stirred for 1hour. Then, cyclohexanone (0.98 g, 10.0 mmol) was dissolved in THF (20mL) and added to the mixture. The mixture was cooled to roomtemperature, stirred for 1 hour, and extracted with DCM and 1N HCl toobtain an organic layer. The obtained organic layer was dried withmagnesium sulfate, and residues obtained by evaporating the solvent wereseparated and purified by silica gel chromatography to obtainIntermediate 1-1 (1.53 g, yield 60%). The produced compound wasidentified through LC-MS. C₁₂H₁₅BrO M⁺ 254.0

Synthesis of Intermediate 1-2

Intermediate 1-1 (2.55 g, 10 mmol), AlCl₃ (1.33 g, 10 mmol), and benzene(10 mL) were added, and the mixture was stirred at 70° C. for 3 hours,cooled to room temperature, neutralized with sodium bicarbonate, andextracted with DCM and water. The obtained organic layer was dried withmagnesium sulfate, and residues obtained by evaporating the solvent wereseparated and purified by silica gel chromatography to obtainIntermediate 1-2 (1.58 g, yield 50%). The produced compound wasidentified through LC-MS. C₁₈H₁₉Br M⁺314.0

Synthesis of Compound 1

Intermediate 1-2 (3.15 g, 10 mmol), N,9-diphenyl-9H-carbazol-3-amine(3.34 g, 10 mmol), tris(dibenzylidene acetone)dipalladium(0) (Pd₂dba₃)(0.46 g, 0.5 mmol), and sodium tert-butoxide (2.88 g, 30 mmol) weredissolved in toluene (60 mL) and then stirred at 80° C. for 3 hours. Thereaction solution was cooled to room temperature, 40 mL of water wasadded thereto, and the mixture was extracted three times with 50 mL ofethyl ether to collect an organic layer. The collected organic layer wasdried with magnesium sulfate, and residues obtained by evaporating thesolvent were separated and purified by silica gel chromatography toobtain Compound 1 (3.98 g, yield 70%). The produced compound wasidentified through MS/FAB and ¹H NMR.

2. Synthesis of Compound 2

Compound 2 was synthesized in substantially the same manner as thesynthesis of Compound 1 by utilizingN-(naphthalen-1-yl)-9-phenyl-9H-carbazol-3-amine instead ofN,9-diphenyl-9H-carbazol-3-amine. The produced compound was identifiedthrough MS/FAB and ¹H NMR.

3. Synthesis of Compound 3

Compound 3 was synthesized in substantially the same manner as thesynthesis of Compound 1 by utilizingN-(naphthalen-2-yl)-9-phenyl-9H-carbazol-3-amine instead ofN,9-diphenyl-9H-carbazol-3-amine. The produced compound was identifiedthrough MS/FAB and ¹H NMR.

4. Synthesis of Compound 21

Compound 21 was synthesized in substantially the same manner as thesynthesis of Compound 1 by utilizing N,9-diphenyl-9H-carbazol-2-amineinstead of N,9-diphenyl-9H-carbazol-3-amine. The produced compound wasidentified through MS/FAB and ¹H NMR.

5. Synthesis of Compound 24

Compound 24 was synthesized in substantially the same manner as thesynthesis of Compound 1 by utilizingN-([1,1′-biphenyl]-4-yl)-9-phenyl-9H-carbazol-2-amine instead ofN,9-diphenyl-9H-carbazol-3-amine. The produced compound was identifiedthrough MS/FAB and ¹H NMR.

6. Synthesis of Compound 34

Compound 34 was synthesized in substantially the same manner as thesynthesis of Compound 1 by utilizingN-(dibenzo[b,d]furan-3-yl)-9-phenyl-9H-carbazol-2-amine instead ofN,9-diphenyl-9H-carbazol-3-amine. The produced compound was identifiedthrough MS/FAB and ¹H NMR.

7. Synthesis of Compound 39

Compound 39 was synthesized in substantially the same manner as thesynthesis of Compound 1 by utilizingN-(dibenzo[b,d]thiophen-2-yl)-9-phenyl-9H-carbazol-2-amine instead ofN,9-diphenyl-9H-carbazol-3-amine. The produced compound was identifiedthrough MS/FAB and ¹H NMR.

8. Synthesis of Compound 41

Compound 41 was synthesized in substantially the same manner as thesynthesis of Compound 1 by utilizing9-(naphthalen-2-yl)-N-phenyl-9H-carbazol-3-amine instead ofN,9-diphenyl-9H-carbazol-3-amine. The produced compound was identifiedthrough MS/FAB and ¹H NMR.

9. Synthesis of Compound 61

Synthesis of Intermediate 61-1

3-bromo-9-phenyl-9H-carbazole (3.22 g, 10.0 mmol),(4-chlorophenyl)boronic acid (1.56 g, 10.0 mmol), Pd(PPh₃)₄ (0.58 g, 0.5mmol), and K₂CO₃(4.14 g, 30.0 mmol) were dissolved in a mixed solution(60 mL) of THF/H₂O (2/1), and the mixture was stirred at 80° C. for 16hours. The reaction solution was cooled to room temperature and thenextracted three times with water (60 mL) and diethyl ether (60 mL) toobtain an organic layer. The obtained organic layer was dried withmagnesium sulfate, and residues obtained by evaporating the solvent wereseparated and purified by silica gel chromatography to obtainIntermediate 61-2 (2.12 g, yield 60%). The produced compound wasidentified through LC-MS. C₂₄H₁₆ClN M⁺353.1

Synthesis of Intermediate 61-2

Intermediate 61-1 (3.54 g, 10 mmol), aniline (1.40 g, 15 mmol),tris(dibenzylidene acetone)dipalladium(0) (Pd₂dba₃) (0.46 g, 0.5 mmol),and sodium tert-butoxide (2.88 g, 30 mmol) were dissolved in toluene (60mL) and then stirred at 100° C. for 3 hours. The reaction solution wascooled to room temperature, 40 mL of water was added thereto, and themixture was extracted three times with 50 mL of ethyl ether to collectan organic layer. The collected organic layer was dried with magnesiumsulfate, and residues obtained by evaporating the solvent were separatedand purified by silica gel chromatography to obtain Intermediate 61-2(3.08 g, yield 75%). The produced compound was identified through LC-MS.C₃₀H₂₂N₂ M⁺410.1

Synthesis of Compound 61

Intermediate 61-2 (4.11 g, 10 mmol), Intermediate 1-2 (3.15 g, 10 mmol),tris(dibenzylidene acetone)dipalladium(0) (Pd₂dba₃) (0.46 g, 0.5 mmol),and sodium tert-butoxide (2.88 g, 30 mmol) were dissolved in toluene (60mL) and then stirred at 80° C. for 3 hours. The reaction solution wascooled to room temperature, 40 mL of water was added thereto, and themixture was extracted three times with 50 mL of ethyl ether to collectan organic layer. The collected organic layer was dried with magnesiumsulfate, and residues obtained by evaporating the solvent were separatedand purified by silica gel chromatography to obtain Compound 61 (4.52 g,yield 70%). The produced compound was identified through MS/FAB and ¹HNMR.

10. Synthesis of Compound 81

Compound 81 was synthesized in substantially the same manner as thesynthesis of Compound 61 by utilizing 2-bromo-9-phenyl-9H-carbazoleinstead of 3-bromo-9-phenyl-9H-carbazole. The produced compound wasidentified through MS/FAB and ¹H NMR.

The ¹H NMR results of the Example Compounds are listed in Table 1:

MS/FAB Compound ¹H NMR(CDCl₃, 400 MHz) found calc. Compound 8.55(d, 1H),7.94(d, 1H), 7.62-7.50(m, 6H), 568.25 568.29 1 7.35-7.00(m, 18H),2.15-1.98(m, 4H), 1.53-1.43(m, 6H) Compound 8.55(d, 1H), 8.22(d, 1H),8.15(d, 1H), 7.94(d, 1H), 618.25 618.30 2 7.81(d, 1H), 7.63-7.49 (m,10H), 7.35-7.13(m, 13H), 2.15-1.98(m, 4H), 1.53-1.43(m, 6H) Compound8.55(d, 1H), 7.94(d, 1H), 7.78(d, 1H), 7.71(d, 1H), 618.25 618.30 37.62-7.14(m, 24H), 2.15-1.98(m, 4H), 1.53-1.43(m, 6H) Compound 8.55(d,1H), 8.24(d, 1H), 7.94(d, 1H), 7.62-7.50(m, 5H), 568.25 568.29 217.35-7.00(m, 18H), 2.15-1.98(m, 4H), 1.53-1.43(m, 6H) Compound 8.55(d,1H), 8.24(d, 1H), 7.94(d, 1H), 7.75(d, 2H), 644.27 644.32 247.62-7.14(m, 25H), 2.15-1.98(m, 4H), 1.53-1.43(m, 6H) Compound 8.55(d,1H), 8.24(d, 1H), 8.03(s, 1H), 7.98-7.94(m, 2H), 658.25 658.30 347.80(d, 1H), 7.62-7.50(m, 6H), 7.39-7.14(m, 15H)6.91(d, 1H),2.15-1.98(m, 4H), 1.53-1.43(m, 6H) Compound 8.55(d, 1H), 8.45(d, 1H),8.24(d, 1H), 7.95-7.93(m, 674.23 674.28 39 3H),7.85(d, 1H), 7.62-7.14(m,21H), 2.15-1.98(m, 4H), 1.53-1.43(m, 6H) Compound 8.55(d, 1H),8.03-8.01(m, 3H), 7.94(d, 1H), 7.83(s, 1H), 618.25 618.30 417.59-7.54(m, 3H), 7.35-7.00(m, 19H), 2.15-1.98(m, 4H), 1.53-1.43(m, 6H)Compound 8.55(d, 1H), 7.99-7.89(m, 3H), 7.77(d, 1H), 644.27 644.32 617.62-7.50(m, 7H), 7.37-7.00(m, 18H), 2.15-1.98(m, 4H), 1.53-1.43(m, 6H)Compound 8.55(d, 1H), 8.31(d, 1H), 7.94-7.91(m, 2H), 7.74(s, 1H), 644.27644.32 81 7.62-7.50(m, 7H), 7.37-7.00(m, 18H), 2.15-1.98(m, 4H),1.53-1.43(m, 6H)

Example Compounds

Comparative Example Compounds

(Manufacture of Organic Electroluminescence Device)

For an anode, an ITO glass substrate of about 15 Ω/cm² (about 1,200 Å)made by Corning Co. was cut to a size of 50 mm×50 mm×0.7 mm, cleansed byultrasonic waves utilizing isopropyl alcohol and pure water for about 5minutes, and then irradiated with ultraviolet rays for about 30 minutesand exposed to ozone and cleansed. The glass substrate was installed ona vacuum deposition apparatus.

On the upper portion of the substrate, 2-TNATA was deposited in vacuumto form a 600 Å-thick hole injection layer, and then an Example Compoundor Comparative Example Compound was deposited in vacuum to form a 300Å-thick hole transport layer.

On the upper portion of the hole transport layer,9,10-di(naphthalen-2-yl)anthracene (hereinafter, DNA) as a bluefluorescent host and DPAVBi as a blue fluorescent dopant wereco-deposited at a weight ratio of 98:2 to form a 300 Å-thick emissionlayer.

Then, Alq3 was deposited on the upper portion of the emission layer toform a 300 Å-thick electron transport layer; LiF which is an alkalinemetal halide was deposited on the upper portion of the electrontransport layer to form a 10 Å-thick electron injection layer; and Alwas deposited in vacuum to form a 3,000 Å-thick LiF/AI electrode(negative electrode), thereby manufacturing an organicelectroluminescence device.

(Evaluation of Organic Electroluminescence Device Characteristics)

TABLE 2 Hole Driving Current Half service transport voltage densityBrightness Efficiency luminous life material (V) (mA/cm²) (cd/m²) (cd/A)color (hr@100 mA/cm²) Comparative X-1 7.01 50 2645 5.29 Blue 258 Example1 Comparative X-2 5.52 50 2780 5.56 Blue 352 Example 2 Comparative X-35.62 50 2815 5.63 Blue 366 Example 3 Comparative X-4 5.83 50 2760 5.52Blue 400 Example 4 Comparative X-5 5.95 50 2625 5.25 Blue 390 Example 5Example 1 Compound 1 5.23 50 3225 6.45 Blue 480 Example 2 Compound 25.36 50 3060 6.12 Blue 510 Example 3 Compound 3 4.96 50 3260 6.52 Blue550 Example 4 Compound 21 5.22 50 3065 6.13 Blue 605 Example 5 Compound24 4.88 50 3145 6.29 Blue 470 Example 6 Compound 34 4.69 50 3065 6.13Blue 510 Example 7 Compound 39 5.15 50 3075 6.15 Blue 412 Example 8Compound 41 4.99 50 3160 6.32 Blue 400 Example 9 Compound 61 5.10 503080 6.16 Blue 405 Example 10 Compound 81 4.91 50 3000 6.00 Blue 550

Referring to the results of Table 2, it may be confirmed that when theamine compound according to an example is included in the hole transportregion, the organic electroluminescence device has low driving voltage,and improved brightness, efficiency, and service life compared to thedevices of the Comparative Examples.

The organic electroluminescence device of an example may achieve highluminous efficiency and a long service life by utilizing the aminecompound represented by Formula 1 as a hole transporting material.

The amine compound of an example may facilitate high luminous efficiencyand a long service life of the organic electroluminescence device.

The organic electroluminescence device according to an embodiment of thepresent disclosure may achieve high efficiency and a long service life.

The amine compound according to an embodiment of the present disclosuremay improve a service life and efficiency of the organicelectroluminescence device.

Although the present disclosure has been described with reference toexample embodiments of the present disclosure, it will be understoodthat the present disclosure should not be limited to these exampleembodiments, and that various changes and modifications can be made bythose skilled in the art without departing from the spirit and scope ofthe present disclosure.

As used herein, the terms “substantially,” “about,” and similar termsare used as terms of approximation and not as terms of degree, and areintended to account for the inherent deviations in measured orcalculated values that would be recognized by those of ordinary skill inthe art.

Any numerical range recited herein is intended to include all sub-rangesof the same numerical precision subsumed within the recited range. Forexample, a range of “1.0 to 10.0” is intended to include all subrangesbetween (and including) the recited minimum value of 1.0 and the recitedmaximum value of 10.0, that is, having a minimum value equal to orgreater than 1.0 and a maximum value equal to or less than 10.0, suchas, for example, 2.4 to 7.6. Any maximum numerical limitation recitedherein is intended to include all lower numerical limitations subsumedtherein and any minimum numerical limitation recited in thisspecification is intended to include all higher numerical limitationssubsumed therein. Accordingly, Applicant reserves the right to amendthis specification, including the claims, to expressly recite anysub-range subsumed within the ranges expressly recited herein.

Accordingly, the technical scope of the present disclosure is notintended to be limited to the contents set forth in the detaileddescription of the specification, but is intended to be defined by theappended claims and equivalents thereof.

What is claimed is:
 1. An organic electroluminescence device comprising:a first electrode; a hole transport region on the first electrode; anemission layer on the hole transport region; and an electron transportregion on the emission layer, wherein the hole transport regioncomprises an amine compound represented by Formula 1:

and wherein, in Formula 1, L₁ and L₂ are each independently a directlinkage, a substituted or unsubstituted arylene group having 6 to 30ring-forming carbon atoms, or a substituted or unsubstitutedheteroarylene group having 2 to 30 ring-forming carbon atoms, m and nare each independently an integer of 0 to 2, Ar₁ and Ar₂ are eachindependently a substituted or unsubstituted aryl group having 6 to 30ring-forming carbon atoms, or a substituted or unsubstituted heteroarylgroup having 2 to 30 ring-forming carbon atoms, R₁ to R₄ are eachindependently a hydrogen atom, a deuterium atom, a halogen atom, a cyanogroup, a substituted or unsubstituted alkyl group having 1 to 20 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30ring-forming carbon atoms, or a substituted or unsubstituted heteroarylgroup having 2 to 30 ring-forming carbon atoms, a and b are eachindependently an integer of 0 to 4, and c and d are each independentlyan integer of 0 to
 5. 2. The organic electroluminescence device of claim1, wherein the hole transport region comprises: a hole injection layeron the first electrode; and a hole transport layer on the hole injectionlayer, and wherein the hole injection layer or the hole transport layercomprises the amine compound.
 3. The organic electroluminescence deviceof claim 1, wherein the amine compound represented by Formula 1 isrepresented by Formula 2:

and wherein, in Formula 2, Ar₁, Ar₂, L₁, R₁ to R₄, n, and a to d areeach independently the same as defined in Formula
 1. 4. The organicelectroluminescence device of claim 3, wherein the amine compoundrepresented by Formula 2 is represented by Formula 3:

and wherein, in Formula 3, Ar₁, Ar₂, L₁, R₁ to R₄, n, and a to d areeach independently the same as defined in Formula
 2. 5. The organicelectroluminescence device of claim 4, wherein the amine compoundrepresented by Formula 3 is represented by Formula 4-1 or Formula 4-2:

and wherein, in Formula 4-1 and Formula 4-2, Ar₁, Ar₂, L₁, R₁ to R₄, n,and a to d are each independently the same as defined in Formula
 3. 6.The organic electroluminescence device of claim 4, wherein the aminecompound represented by Formula 3 is represented by Formula 4-3 orFormula 4-4:

and wherein, in Formula 4-3 and Formula 4-4, Ar₁, Ar₂, L₁, R₁ to R₄, n,and a to d are each independently the same as defined in Formula
 3. 7.The organic electroluminescence device of claim 1, wherein L₁ is adirect linkage, a substituted or unsubstituted phenylene, or asubstituted or unsubstituted naphthylene.
 8. The organicelectroluminescence device of claim 1, wherein L₁ is represented byFormula 5:


9. The organic electroluminescence device of claim 1, wherein Ar₂ is asubstituted or unsubstituted aryl group having 6 to 16 ring-formingcarbon atoms.
 10. The organic electroluminescence device of claim 9,wherein Ar₂ is a substituted or unsubstituted phenyl group, asubstituted or unsubstituted naphthyl group, a substituted orunsubstituted biphenyl group, or a substituted or unsubstitutedphenanthrenyl group.
 11. The organic electroluminescence device of claim1, wherein Ar₂ is a substituted or unsubstituted dibenzofuranyl group ora substituted or unsubstituted dibenzothiophenyl group.
 12. The organicelectroluminescence device of claim 1, wherein Ar₁ is represented byFormula 6:

and wherein, in Formula 6, R₅ is a hydrogen atom, a deuterium atom, ahalogen atom, a cyano group, a substituted or unsubstituted alkyl grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 ring-forming carbon atoms, or a substituted orunsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,and e is an integer of 0 to
 5. 13. The organic electroluminescencedevice of claim 1, wherein the amine compound represented by Formula 1is any one selected from the compounds represented by Compound Group 1:


14. An amine compound represented by Formula 1:

wherein, in Formula 1, L₁ and L₂ are each independently a directlinkage, a substituted or unsubstituted arylene group having 6 to 30ring-forming carbon atoms, or a substituted or unsubstitutedheteroarylene group having 2 to 30 ring-forming carbon atoms, m and nare each independently an integer of 0 to 2, Ar₁ and Ar₂ are eachindependently a substituted or unsubstituted aryl group having 6 to 30ring-forming carbon atoms, or a substituted or unsubstituted heteroarylgroup having 2 to 30 ring-forming carbon atoms, R₁ to R₄ are eachindependently a hydrogen atom, a deuterium atom, a halogen atom, a cyanogroup, a substituted or unsubstituted alkyl group having 1 to 20 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30ring-forming carbon atoms, or a substituted or unsubstituted heteroarylgroup having 2 to 30 ring-forming carbon atoms, a and b are eachindependently an integer of 0 to 4, and c and d are each independentlyan integer of 0 to
 5. 15. The amine compound of claim 14, wherein theamine compound represented by Formula 1 is represented by Formula 2:

and wherein, in Formula 2, Ar₁, Ar₂, L₁, R₁ to R₄, n, and a to d areeach independently the same as defined in Formula
 1. 16. The aminecompound of claim 15, wherein the amine compound represented by Formula2 is represented by Formula 3:

and wherein, in Formula 3, Ar₁, Ar₂, L₁, R₁ to R₄, n, and a to d areeach independently the same as defined in Formula
 2. 17. The aminecompound of claim 16, wherein the amine compound represented by Formula3 is represented by Formula 4-1 or Formula 4-2:

and wherein, in Formula 4-1 and Formula 4-2, Ar₁, Ar₂, L₁, R₁ to R₄, n,and a to d are each independently the same as defined in Formula
 3. 18.The amine compound of claim 16, wherein the amine compound representedby Formula 3 is represented by Formula 4-3 or Formula 4-4:

and wherein, in Formula 4-3 and Formula 4-4, Ar₁, Ar₂, L₁, R₁ to R₄, n,and a to d are each independently the same as defined in Formula
 3. 19.The amine compound of claim 14, wherein Ar₂ is a substituted orunsubstituted aryl group having 6 to 16 ring-forming carbon atoms. 20.The amine compound of claim 14, wherein the amine compound representedby Formula 1 is any one selected from the compounds represented byCompound Group 1: